What I Should Have Done
by TerraBeth
Summary: One-shot.  Chuck and Jenny, but not a Chenny fic.  My exploration of the tragedy that was 3x22.  This is dark and angsty.  Consider yourself forewarned.


**A/N: In this fic, I reference a couple of clips from the show that were ultimately deleted. You can watch them here if you like: (w w w . y o u t u b e).com/watch?v=GZ4RwCUIsjk (w w w . y o u t u b e).com/watch?v=fdhZhc9GFXU.**

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><p>Staring at the rivulets of rain that ran down the window like tears, she considered the boy who was her first kiss. Her first sex.<p>

But not her first love.

—

No one had ever looked at her like that before. With such undisguised _wanting_. Oh, she knew, even then, that she shouldn't have snuck off with him, but she was oh-so-excited, oh-so-scared. On that evening she had looked in the mirror and realized she was beautiful, and she fell under the spell of herself, the same spell that plainly struck the older boy in the patterned silk scarf a few hours later.

Then they were alone, and her back was against the wall, and she heard herself making excuses. Panic seized her, but only for a moment, and then he was suddenly gentle, offering her champagne, apologizing for moving too quickly. And the panic faded, to be replaced with a tinge of regret that rose from her chest like a dying wisp of smoke.

There went her first kiss. And she was never going to get it back.

—

It was all Serena's fault—at least, that's what he thought back then. The bile rose in the back of his throat when he remembered how she had rejected him. Who the hell was _she_ to act like he was somehow beneath her?

And so his eyes scanned the ballroom, searching for a girl who would easily surrender herself to him.

He needed to forget. Needed not to think about how _unwanted_ he was. Not just by Serena—by everyone.

And look—there was a pretty young thing with huge blue eyes, a wobbling mouth, and a round doll's face. And when he spoke to her she stammered like a servant. Perfect.

He had simply assumed that any girl who went into a dark corner with Chuck Bass knew what she was getting into. He hadn't thought that such naiveté existed.

At least not any longer.

(At least not on the Upper East Side.)

So when she backed away from his mouth and made some lame excuse about wanting to go back to the party, he was confused for a moment. But he figured she was teasing him, that she was holding back so as to maintain some small semblance of virtue.

He should have taken her at face value.

But he shifted tactics. He treated her like a young mare that was yet unbroken. He spoke to her in a gentle voice. He plied her with sweet, sweet champagne. He corralled her up on the rooftop and with his knee he directed her gangly legs apart.

Oh, he should have just gone after a girl with a bit more Eve in her eyes. Or—he should have just backed off and left her alone before he got a black eye for his trouble.

Funny. He didn't know what it was about her—he had never been able to put his finger on it. But Jenny Humphrey just had a knack for bringing out the absolute worst in him.

—

In spite of everything, she still wanted to impress him. She even let it slip, stupidly, that she had sewn her own dress, and he looked at her with astonishment and said, "You're a clever little thing, aren't you?"

And she blushed at the compliment.

When he invited her up to the rooftop, she agreed, and in the back of her mind she was planning how it would work out—he'd kiss her a couple more times, and then Dan would come up and pitch a fit, and she'd roll her eyes, and say "Omigod, Dan, don't be so dramatic, I'm _fine_!" and Dan-the-protector would take her home in a huff, and the next day Chuck Bass (_the_ Chuck Bass) would ask about her at school, and then he would walk her down the path to Constance, and he would purr things in her ear in that low sexy voice of his, and she'd have the slow steady high school romance that every girl was supposed to have.

At least, that's what all the films and books had promised her.

That every boy, at heart, was patient. _Kind_.

But then his hands were pawing at her breasts and her heart was beating so fast she thought she might die and _this wasn't the way that it was supposed to happen_ and she was terrified of him and of her own desire for him, and when she said "No, _stop_" and he ignored her, part of her—she felt sick to admit it now—part of her was _flattered_ that he wanted her that much (because, after all, "no" was just something that good girls were _supposed_ to say) but she couldn't do it, just couldn't do it, and she panicked and whined at him: "No!"

She shouldn't have acted like a scared little girl. She should have pushed him away with fire in her eyes and strength in her voice. Lifted her chin and stared him down like a queen, and told him that she wasn't his plaything.

But instead she stood there, frozen and trembling, and her back was against the wall again and his hands were pinning her wrists and his knee was nudging apart her knees and strangely enough her biggest concern at the time was not that he was stronger than her or that she was alone and helpless but that she was on the verge of tears and she didn't want him to see her cry.

_Please God. Don't let him see me cry._

—

She remembered the weeks after their encounter on the rooftop, when he still cared enough to taunt her. He shot her predatory looks across the courtyard at school; he mouthed obscene "hellos" to her over Nate's shoulder, his lips undulating the words as they'd undulated against her soft white skin.

For a while, he seemed to relish any and every opportunity to remind her of what a pathetic little virgin she was.

(But that was before Blair Waldorf had laid claim to his heart and soul.)

So when she walked into the Empire penthouse and saw him sitting in the darkness, regarding his amber glass of scotch with glazed-over eyes, he didn't even have to say it; she knew what he thought of her. That she couldn't possibly know the depths of the pain he was feeling.

But she _did_ know what pain was, and she wanted to prove it, so when Chuck offered her the glass, she didn't reject it. She took it, even though she knew she shouldn't have, because it already felt like they were complicit in something.

At that moment she realized that, over the past couple of years, Chuck Bass had become a man. But she was still a little girl.

And maybe that was because her father was still alive. And she still _loved_ her father, _needed_ her father, even though whenever she looked at him lately she was practically beside herself with equal parts rage and shame.

Because she was sick of it. Sick of being daddy's little girl. Sick of being sexually policed. Sick of being treated as if she didn't have the right to decide what she did with _her own body._

"You don't need protecting," Chuck had said to her a couple of weeks earlier. "You've grown up. I see it even if Nate doesn't."

But he was wrong. However much she hated to admit it, she _did_ still need protection from all the snares and traps of this world.

Case in point—when Chuck's fingertips brushed against hers, it was like lightning striking her core.

And when he leaned into her and opened his mouth against hers, when his hand slid up her skirt between her legs (farther than even Damien's had ever gone) and stroked the cleft of her sex through her panties—she let it happen.

She knew, even then, that she and Chuck, in the darkest recesses of their souls, were mirror images of each other. It just wasn't in their nature to give, give, give without reprieve, to freely offer themselves to other people as if they were pouring water onto sand.

Maybe that's why it was such a relief for them to fall into each other's arms. _There_, they weren't expected to give. There, there was an implicit understanding that all they would do—at least, when it came each other—was _take_.

And that was all right with her.

—

Her only allowance to her nerves was to ask him if she could hop in the shower. "Go ahead," he growled at her, and she could tell from the tone of his voice that he thought she was going to chicken out.

(Well, she was going to prove him wrong.)

She used Nate's bathroom. She stood under the stream of hot rivulets, her skin turning pink. She half-scalded herself, as though taking part in some improvised rite of passage.

She used Nate's body-wash; she enveloped herself in his citrus-y scent, as though she were saying one final goodbye to the dream of his love.

He was the only boy she'd ever known who really might be _that_ patient, that _kind_, like those dream-boyfriends in the books and films. The kind that didn't exist in real life.

(Or, if they _did_, then they didn't want you _back.)_

She didn't wash her face, because her make-up was the mask that she needed to hide behind. It made her feel safe. Protected.

She should have. Washed her face, that is. Because if she _had_, as soon as she approached the bed where Chuck laid, waiting for her, then he would have seen how young and hapless she truly was.

And maybe then things would have ended differently.

—

As soon as he pulled off her flimsy black negligee, he instantly recognized the scent rising from her body. That strange burnt-grapefruit smell.

What he should have said was this: "Jenny—I don't think I can do this."

"Wh-_what_? Why?" she would have replied in a shaking voice, and he would have answered laconically, "Because right now you smell just like _Nate_."

And she would have grunted "Hello, Chuck," in the deepest, most Nate-like voice she could muster, and then they would have both laughed to the point of hysteria, and as soon as he was able to speak again he would have said helplessly "What are we doing, Jenny?" and she would have said "I don't know" and he would have said "Let's just go smoke some weed and watch a stupid movie." And she would have agreed.

And then, maybe then, when Blair walked into the apartment, Chuck and Jenny would have been innocently sharing a joint, laughing as the squirrels chased each other 'round the tree-tops in _The Sword in the Stone_.

"Chuck. What in God's name are you doing with _Jenny Humphrey_?" she would have said in disgust. And Jenny would have recognized that this was serious, serious business indeed, and she would have slunk off to Nate's room to give them some privacy.

And he would have said to Blair, "Well. It was either hang out with Jenny Humphrey or jump off the balcony. So I'm hanging out with Jenny Humphrey."

"Don't make jokes like that, Chuck," Blair would have said in alarm.

"I'm not joking, Blair," he would have replied.

That's what the scotch had been for. To steady his nerves. Because when he had first come back from the Empire State Building, he had gone straight to the balcony, stepped up on the railing, and looked down at the pavement below. And all he had been able to think was "Will I die before or after I hit the ground?"

_Before or after? Before or after?_

The question had churned like a wheel in his brain. And so he had decided to drink until the answer became irrelevant.

But his fantasy-Blair wouldn't have known that, and she would have never needed to know. Because at that moment she would have brought the peonies out from behind her back and have given the bouquet a little twirl, and she would have smiled at him with tears in her eyes, and he would have said, in a voice filled with wonder and gratitude, "You _went_," and he would have risen to meet her, and they would have kissed, and—

—

Instead, there he was, lying between Jenny Humphrey's legs and fumbling at her cunt, and when he looked down at her to ask what was going on he saw that she was hiding her face behind her hands.

"Chuck—" she said in a strangled voice. "I have to tell you—I'm—I'm a virgin. I mean, I still want to do it, but—"

He paused for a moment to process this information. He had thought that she and Damien—well. They must not have gone through with it.

Well. This was certainly an unexpected turn of events.

But the emotion that rose within him when he looked at the face of the scared girl underneath him was not sympathy. It was _annoyance_.

Because what he needed right now, more than he had ever needed anything from another human being, was to be inside of her.

He needed to forget the pain that was ripping his soul apart.

Of course, what he _should_ have done—if he had been able, somehow, to ignore the fact that there was an abyss inside of him where his heart had once been, if he had been able to _pretend,_even if only for a couple of minutes, that he was a good guy, or an average guy, or maybe even a slightly _less_than average guy—was to say, "Christ, Jenny. We can't. You—you don't want to do this."

And then she would have cried hot tears of shame, and she would have said in a tremulous voice, "Don't you want me?"

And maybe, in this fantasy world in which he was actually a halfway decent person, he would have been able to reassure her, tell her that she was beautiful, she was smart, she was worth more than a quick sloppy fuck in the dark.

But instead, to his infinite horror and regret, what came of his mouth was a single word, laden with scorn, as if the information she'd just shared was completely irrelevant to their present situation:

"Okay."

—

Chuck Bass did not have a lot of experience with virgins.

In spite of his bluster, his lewdness, and his occasional moments of sexual aggression, he had never been one to seek out inexperienced women. It seemed a truth universally acknowledged that they were far more trouble than they were worth.

The only other time he could even _remember_ seducing a virgin was his first time with Blair—after she had turned around on the stage and looked over her shoulder at him, like Eve having just tasted the most delicious of apples, and he had looked up at her with lips parted like the pages of a Bible unfurled.

It seemed as though the scales had suddenly fallen from their eyes, and they had looked at each other for what felt like the very first time.

And then, they were in the back of his limo, and her bare thighs were against his bare thighs, and her small breasts, cheekily upturned, were soft and ripe against his lips and tongue, and her hair was cascading over her pale bare shoulders like a waterfall over smooth white stones, and her face, illuminated by the darting-by lights of Manhattan at night, was a cloud of luminescent fireflies, and she was looking at him, awed by him—God, she seemed already halfway _in love_ with him.

She was altogether like the virginal young Eve, and he was her Adam, and it truly seemed to him that this must have been the first time in the history of the world that anyone had ever felt a desire so tremendous. Because if this happened to everyone, _every day,_towers would fall, buildings would collapse, and everyone would drop to the ground and fuck endlessly in the ruins of what had once been civilization.

And her hands gliding over his face were dove's wings and his rigid cock was an ember burning between her thighs.

His heartbeat an arpeggio.

Her eyes incandescent stars.

—

And there he was, once again, on the other side of forgetting. And he was fucking Jenny Humphrey like a bull rutting a cow.

_I will never hold her again_, he thought, as Blair's sweet oval face loomed in his memory.

_I will never touch her again._

And just as he was wondering if there were any way that he could bear this, if there were any way that he could possibly go on living having lost her, he choked back a sob—and he realized with a jolt of anger at himself that Jenny must have noticed.

_Do not let her see you cry_, he ordered himself, and he gave his head a quick jerk to the side as if he were giving himself a hard, painful slap to the face, and even though he knew that he must be hurting the girl underneath him, whose soft sobs he could hear, he began to fuck her faster, harder.

Anything to hasten towards the nothingness on the other side of orgasm. Anything to get to the oblivion inside of her.

—

When she saw that he was fighting back tears, she should have stopped him. She should have said his name gently, should have wrapped her arms around him.

She should have let him cry against her naked shoulder just as she was longing to cry against his, and, lost souls that they were, they could have mourned together for all that they had lost.

But she didn't. She didn't even look at him at all. She just stared over his shoulder at the ceiling, her tears tracking black paths down her cheeks.

In spite of the pain, in spite of the acrid scent of sweat and blood that arose from the joint of their coupling, this was exactly what she needed.

She let it happen, let him fuck her, because the pain felt right. Fitting. Like something she deserved.

—

When he was done, he immediately left the bedroom and went to take a shower.

He washed off her scent. It had weirdly mingled with the scent of Nate, and the smell hit his nostrils like an angry reproach.

With a sponge he wiped the dabs of blood off of his crotch and thighs.

_What's done cannot be undone_, he thought as he watched the faint red trail disappear down the drain, and he gave a little laugh, and he felt as though he were going to be sick.

"Are you okay?" he managed to croak at her when he walked back into the bedroom. And she didn't answer him, and he was grateful, because he knew what she would have said if she had.

"You're welcome to stay the night," he mumbled. And though he knew that it was far too little, far too late, he took the tiniest bit of comfort in the fact that he'd finally done what he should have done.

Because—truth be told—he wanted nothing more than for her to leave, for her to go away and never come back, because he couldn't take it, couldn't take the guilt of seeing her devastated face, seeing her lie there. Emptied. Hollowed out.

Like the ghost of a girl he had just killed.

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><p><strong>AN: As always, I'd love to hear your thoughts. Please review!**


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